Dimethylformamide dimethyl acetal → 3-Chloro-6-(-3-dimethylamino-acryloyl)-pyridine-2-carbonitrile

HRID 55896Notes

Reaction equation

HRID 55896 reaction equation
[C:1]([C:4]1[N:9]=[C:8]([C:10]#[N:11])[C:7]([Cl:12])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].CO[CH:15](OC)[N:16]([CH3:18])[CH3:17]>C1(C)C=CC=CC=1>[Cl:12][C:7]1[C:8]([C:10]#[N:11])=[N:9][C:4]([C:1](=[O:3])[CH:2]=[CH:15][N:16]([CH3:18])[CH3:17])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 903566946-Acetyl-3-chloropyridine-2-carbonitrile

Product 1

HCID 1186200273-Chloro-6-(-3-dimethylamino-acryloyl)-pyridine-2-carbonitrileYield 35%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Compound 64 (633 mg, 2.7 mmol) and N,N-dimethylformamide dimethyl acetal (1.1 mL, 8.1 mmol) in toluene was heated to reflux for 5 h. After which time the solvent was evaporated and the crude product triturated with isoxane/diethylether to give compound 67 as an orange solid (222 mg, 35%); LCMS Rt=2.35 min (MeOH-FA method), m/z 236 (MH+).

Workup

  1. temperatureto reflux for 5 h
  2. customAfter which time the solvent was evaporated
  3. customthe crude product triturated with isoxane/diethylether

Sources & evidence

ORD record
ord-d8324f398a0c4032b9f244b496ce199f
Source dataset
uspto-grants-2016_09
Patent number
US09433622B2

Reaction notes

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